City Diaries

Ryan Plett's Chicago

The blogger behind You Have Broken the Internet takes us on a tour of his favorite Second City spots.

Belmont Barbershop. This is my spot in Chicago for a great cut and a hot shave, both of which will only cost around $30 or less, each. Ask for Jesse if you like vintage Ford’s and whiskey.

Haberdash. Haberdash has been in Chicago for quite some time but recently changed their direction a bit with the product mix, bringing in quality brands like Alden, L.B.M. 1911, Barbour, Walk-Over, Tanner Goods, 3sixteen, etc.  They have some great new things in the works that should continue to improve the way men dress here.

Lincoln Park & Lakefront Trail. Lincoln Park and its surrounding neighborhood are directly located on Lake Michigan and provide an amazing 18-plus miles of biking and running, as well as a free public zoo, golf course, sports fields, gardens, and museums.  Definitely a nice escape from the city hustle.

Lou Mitchell’s. This is the classic breakfast spot in Chicago: Double yolk eggs, fresh pastries, and at least one person in city government—in the corner booth—looking all mafia’d out.  Presidents, actors, and your typical group of old men drinking coffee and reading the paper are all standard fare at this Loop diner.  Go early if you want pastry, it’ll be gone by 10am on the weekends.

Clark Street Ale House. I love this spot, old as hell and it only serves beer and liquor. If you need food you better hit something before stopping at this River North establishment.


Gilt Bar. This is a fairly new restaurant, a few blocks from me in River North, and already a Michelin-rated spot for its amazing food and custom cocktails [Ed.: not to mention its catchy name].  The speakeasy in the basement has more Horween leather than a shoe factory with its custom wall of Chesterfield couches (just bring cash when you head downstairs, no credit cards are accepted).

Longman & Eagle. This is easily one of my favorite spots in Chicago and I’m almost glad I live kind of far from the Logan Square bar, restaurant, and hotel (I’d probably be broke and try to live there if I was any closer).  An awesome ever-changing menu, bad ass bartenders that take an insane amount of pride in their craft, and a boutique hotel that is completely furnished with custom furniture and locally-made art.


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